Monoazo dyestuffs



Patented Oct. 8, 19 29,

UNITED- STATES mE BEBEB AND JOSEPH SPIELER, OF BASEL, SWITZERLAND, ASSIGI IOBS TO SOCIETY PAT-ENT- OFFICE or cmmrcar. INDUSTRY IN BASLE, or BAsEL, swr'rznnmnn monoazo mrns'rnrrs I llo Drawing. Application filed l iovcmber 22, 1927, Serial R0. 235,1 12, and in Switzerland December 4,

The present invention relates to; new

d estufis which are particularly valuable i orv the production of fast'tints on animal fiber. It comprises the new dyestuffs, the process of We have found that new yellow pyrazolones azo-dyestufis are obtained which correspond with the general formula acidylNH RN =N-P wherein It means an aryl nucleus of the henzene series which contains a sulfonic group in 'ortho position and the acidyc-group 1n the residue of a l-aryl-5-pyrazolone, by coupling diazo-compounds of ;the''=--'general f l r 1 I I acidyl -NH 'RN=N OH,

wherein R has the above mentiened'signification, ,with 1 -aryl-5-pyrazolone.

,These new azo-dyestufl's, which form yellow to brown-yellow and orange-yellow Powders, dissolving in water onaddition 0 sodium 7 carbonate solution with yellow color, dye

.wool or animal fibers uniformly throughout, yielding dyeings of excellent fastnessto light. According to the choice of'the components fast to water but also to acid fulling and to alkali and, under certain conditions, have good fastness to washing. The technical ad vancein the invention is due to the existence of all these pro erties in one and the same ydyestufi'. Anot er "advantage .of the process resides in the fact that even the 1-ar 1-5- pyrazolone 3-carboxylic acids, which ave yielded hitherto azo'dyestuflsmeta-position to the azo-group, and-P means 'xylidine sulfonic acid dyestuffs are obtained which are not only Ihe pyrazolones applicable as coupling components comprise those which are obtain able from aceto-acet ic ester or oxalo-acetic,

ester and hydrazine or hydrazine compounds. Among these latter may be mentioned articularly. those which, are derived aniline, o-chloraniline, m-chloraniline, mmtraniline, o-toluidine, p-xylidine,. sulfanilic acid, toluidine sulfofiic acid- Y CH,:CH,:NH,:SO,H- 1:f4:2:5 and 1': 5 2 4, chloraniline sulfonic acid Cl:NH,: SO,H= 1:2: 4-

and, the corresponding chloraniline sulfonic acid sulfainide, di-

the naphthylam ine disulfonic acids 1:5:7, 2=3=,6,.2=4:7 and 25,7, and so am The following examples illustrate the in:

vention, the parts being-by weight Emample I I I 28.4 parts of 1-para-sulfophenyl 5-pyrazolone-3-carbo 'lic acid are dissolved in 150 parts of water y means of'20 parts of calcined sodium carbonate. The solution is cooled with iceand mixed with the diazo- Y compound from 23 parts of et acetyl-amino- The dyestufi' thus obtained is a yellow pow:

der it dyes wool in a sulfuric acid bath very uni orm'powerful tints, similar to those of tartrazine i. e. thepyrazolone dyestufi of the in the aryl nucleus the pyrazolone which is formula The dyeings are of very good fastness to light, water and alkali and withstand acid fulling. The formula of the new dyestulf corresponds very probably with the following one 0 n g cHaooHN -N=NX ur-Osom SOaH L=N OOH , methyl-4-acetyliamino-2l-aminm1-benzenesu'lfonie acid, or the compound chlorinated in 5- position, yield similar dyestuffs with l-sulfoaryl-5-pyrazolone-3-carboxylic acid.

With similar final results, the formyl-compounds or the urethanes or the oxalyl-compounds of the said diamino-sulfonic acids may be used as diazotizing components. As improvement of the fastness' to washing of the dyestufis may be secured by using as diazo-,

tizing components those which contain an aromatic nucleus in the acidyl residue, such as benzoyl-, phthalicor arylsulfonic acid derivatives. a

Example 2 of the new dyestufi corresponds very probably with the following one E soul A similar product is obtained when there is substituted for the pyrazolone chlorinated com ounds.

obtainable from .1-amino-2-para-toluenesulfone-5-benzenesulfonic acid and aceto-acetic ester, or if urethane or formylor oxalyl-compounds are substituted for the acetyl-compound. In these cases also the fastness to washing can be enhanced by using benzoyl- The pyrazolones which are derive from unsulfonated bases, such as aniline, ortho-toluidine and xylidine, yield dyestufi's which have a remarkable fastness to washing. Particularly worthy of mention are for example the dyestufis from 4-benzoyl-amino- 2-diazo-l-benzenesulfonic acid and the 1- phenylor 1-(2-chloro) -phenyl-3-methyl-5- pyrazolones.

What we claim is 1. As new products the of the general formula wherein R means an aryl nucleus of the benzene series which contains a sulfonie group in ortho-position and the acidyl-NH-group in meta-position to the azo-group, and wherein 1 means the residue of a 1-aryl-5-pyrazolone, which are obtained by coupling'diazo-compounds of the general formula:

yellow azo-dyestufi's wherein R has the above mentioned signification, with l-aryl-5-pyrazolones, which form yellow to brown and orange-yellow powders, dissolving in water on addition of sodium carbonate solution with yellow color, and dyeing wool in very equal yellow tints which are particularly characterized by their good to very good fast-mess to alkali and light.

2. As new products the yellow azo-dyestufi's of the general formula:

wherein P means the residue of a 1-aryl-5- pyrazolone, which are obtained by coupling diazo-compounds of the general formula:

acidyl-NH N=N--OH wherein P means the residue of a 1-aryl-5- pyrazolone the aryl nucleus of which belongs to the benzene series, which are obtained by couplingdiazo compounds of the general formula:

with such 1-aryl-5-pyrazolones the arylnucleus of which-belongs to the benzene series,

which form yellow to brown and orangeyellow powders, dissolving in water on addition of sodium carbonate solution with yellow color, and dyeing'wool in very equal yellow tints which are particularly characterized by their good to very good fastness to alkali and light.

4. As new products the yellow azo-dyestuifs of the general formula:

ooH the aryl nucleus of which belongs to the benzene series,-\which are obtained by coupling diazo-compounds' of the general formula:

with such 1-aryl-5-pyrazolone-3-carboxylic acids the aryl'nucleus of which belongs to the benzene series, which form yellow to brown and orange-yellow powders, dissolving in water on addition of sodium carbonate solution with yellow color, and dyeing wool in very equal yellow tints which are particularly characterized by their good to very good fastness to alkali and light.

5. As new products the yellow azo-dyestufis of the general formula:

the aryl nucleus of which belongs to the henzene series, which are obtained by coupling the diazo-compound of the formula:

- CHa-G O-NH N=N--OH with such 1-aryl-5-pyrazolones the aryl nucleus of which belongs to the benzene series,

which form yellow to brown and orangeyellow powders, dissolving in water on addition of sodium carbonate solution with yellow color, and dyeing wool in very equal yellow claim 6.

tints which are particularly characterized by ihelilr good to very good fastness to alkali and ig t. y

6. As new products the yellow azo-dy'estufis of the general formula o H t om-oo-NH N=N- N-ary1 the aryl nucleus of whichbelongs to the benzene series and contains as substitutent at least one sulfonic group, which are obtained by coupling the diazo-compound of the formula CHr-CO-NH N=NOH claim 2.

9. Material dyed with the dyestuffs of claim 3. p v I 10. Material dyed with the dyestufis of claim 4.

11. Material dyed with the dyestuffs of claim 5.

12. Material dyed with the dyestuffs In witness whereof we have hereunto signed our names this 10th da of November, 1927.

, E ILE REBER.

JOSEPH SPIELER. 

